Triethylamine → 3-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-N-ethyl-2-hydroxy-N-methoxy-benzenesulfonamide

HRID 2066016ノート

反応式

HRID 2066016 の反応式
[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:6]([OH:16])[C:5]([NH:17][C:18]2[C:21](=O)[C:20](=[O:23])[C:19]=2[O:24]CC)=[CH:4][CH:3]=1.[NH2:27][C@@H:28]([CH2:30][CH3:31])[CH3:29].C(N(CC)CC)C>CC#N.CCO>[C@H:28]([NH:27][C:21]1[C:20](=[O:23])[C:19](=[O:24])[C:18]=1[NH:17][C:5]1[C:6]([OH:16])=[C:7]([S:8]([N:11]([CH2:12][CH3:13])[O:14][CH3:15])(=[O:10])=[O:9])[C:2]([Cl:1])=[CH:3][CH:4]=1)([CH2:30][CH3:31])[CH3:29]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2724537(R)-sec-butylamineHCID 866386316-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

生成物 1

HCID 446291483-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-N-ethyl-2-hydroxy-N-methoxy-benzenesulfonamide

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of 6-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide (Intermediate FA) (100 mg, 0.25 mmol) in MeCN (1 ml) and EtOH (1 ml) was added (R)-(−)-2-Aminobutane (30.7 mg, 0.42 mmol) followed by triethylamine (69 μl, 0.49 mmol). The reaction mixture was heated at 70° C. for 1 hour. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl (aq) and concentrated in vacuo. The residue was triturated with DCM to give a white solid; [M+H]+ 432.2. 1H NMR (DMSO) 0.9 (3H, t, CH3), 1.2 (6H, m), 1.5-1.6 (2H, m), 3.3 (2H, m), 3.7 (3H, s, CH3) 4.1 (1H, m), 7.3 (1H, d), 8.1 (1H, d), 8.3 (1H, d), 9.4 (1H, s), 10.1 (1H, s).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with 1M HCl (aq)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with DCM
  6. customto give a white solid

出典と根拠

ORDレコード
ord-d6af9e0dcc1642919dd68f9bc9dac738
出典データセット
uspto-grants-2012_10
特許番号
US08288588B2

反応ノート

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